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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1837.
Published online 2008 August 30. doi:  10.1107/S1600536808025397
PMCID: PMC2960623

(2R,3aR,4S,7R,7aS,9R,10aR,11S,14R,14aS)-rel-3a,4,7,7a,10a,11,14,14a-Octa­hydro-4,14:7,11-diep­oxy-2,9-propanona­phtho[1,2-f:5,6-f′]diisoindole-1,3,8,10-tetrone (9CI): a cyclo­phane derived from naphtho[1,2-c:5,6-c]difuran

Abstract

The title compound, C25H18N2O6, is a naphthalenophane styled in the manner of Warrener’s alicyclic cyclo­phanes or mol­ecular racks wherein a trimethyl­ene tether is perfectly staggered between the two N atoms such that the central methyl­ene H atoms point toward the naphthalene π-system. The dihedral angle between the mean planes of the two benzene rings is 7.61 (7)°.

Related literature

For related literature, see: Butler et al. (2000 [triangle]); Thibault et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1837-scheme1.jpg

Experimental

Crystal data

  • C25H18N2O6
  • M r = 442.41
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-64-o1837-efi1.jpg
  • a = 21.635 (9) Å
  • c = 8.262 (2) Å
  • V = 3867 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 173 (2) K
  • 0.35 × 0.12 × 0.12 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1997 [triangle]) T min = 0.962, T max = 0.987
  • 7455 measured reflections
  • 4303 independent reflections
  • 3077 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.107
  • S = 1.02
  • 4303 reflections
  • 298 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SAPI91 (Fan, 1991 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025397/lh2675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025397/lh2675Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound, (1), was prepared by the Diels-Alder reaction of naphtho[1,2 - c:5,6 - c]difuran (2) and 1,3-bis(maleimido)propane (3) (see Fig. 2). It is a naphthalenophane styled in the manner of Warreners alicyclic cyclophanes or molecular racks. (Butler et al., 2000) The X-ray structure shows that the three carbon methylene tether is perfectly staggered between the two N atoms such that the central methylene protons point toward the naphthalenic π-system. There is a slight 'warp' to the naphthalene rings system with a mean-planes angle between the two benzene rings being 7.61 (7)°. The only anomalous bond angle in the molecule appears in the methylene tether with the central angle (C23—C24—C25) expanded to 115.17 (13)°, evidence of a repulsive interaction with the naphthalene ring.

Experimental

The preparation of the title compound has been reported (Thibault et al., 2003).

Refinement

Though all the H atoms could be distinguished in the difference Fourier map the H-atoms were included at geometrically idealized positions and refined in riding-model approximation with the C—H distances set in the range 0.95 - 1.00 Å, and Uiso(H) = 1.2 Ueq(C). The final difference map was free of any chemically significant features.

Figures

Fig. 1.
ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.
Fig. 2.
The formation of the title compound.

Crystal data

C25H18N2O6Z = 8
Mr = 442.41F000 = 1840
Tetragonal, P42/nDx = 1.520 Mg m3
Hall symbol: -P 4bcMo Kα radiation λ = 0.71073 Å
a = 21.635 (9) ÅCell parameters from 3862 reflections
b = 21.635 (9) Åθ = 1.0–27.5º
c = 8.262 (2) ŵ = 0.11 mm1
α = 90ºT = 173 (2) K
β = 90ºNeedle, colorless
γ = 90º0.35 × 0.12 × 0.12 mm
V = 3867 (2) Å3

Data collection

Nonius KappaCCD diffractometer4303 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 173(2) Kθmax = 27.5º
ω and [var phi] scansθmin = 1.3º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)h = −27→28
Tmin = 0.962, Tmax = 0.987k = −19→19
7455 measured reflectionsl = −9→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.107  w = 1/[σ2(Fo2) + (0.0461P)2 + 0.9086P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4303 reflectionsΔρmax = 0.19 e Å3
298 parametersΔρmin = −0.18 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.22246 (5)0.13740 (6)0.23245 (15)0.0336 (3)
O20.01829 (5)0.13616 (6)0.36524 (14)0.0309 (3)
O30.16200 (5)0.15123 (5)0.75206 (13)0.0272 (3)
O40.19993 (5)−0.19809 (5)0.40461 (14)0.0273 (3)
O50.22497 (6)−0.07494 (6)−0.02726 (16)0.0399 (3)
O60.03367 (5)−0.10018 (6)0.19059 (15)0.0328 (3)
N10.11727 (6)0.13315 (6)0.26487 (16)0.0227 (3)
N20.12520 (6)−0.07665 (6)0.06537 (16)0.0244 (3)
C10.17687 (7)0.14753 (7)0.3135 (2)0.0244 (4)
C20.17425 (7)0.17364 (7)0.4820 (2)0.0235 (4)
H20.19430.21520.48820.028*
C30.10474 (7)0.17687 (7)0.52369 (19)0.0236 (4)
H30.09070.22030.54200.028*
C40.07282 (7)0.14768 (7)0.38054 (19)0.0232 (4)
C50.19873 (8)0.12925 (7)0.6167 (2)0.0241 (4)
H50.24450.13020.63390.029*
C60.10185 (7)0.13748 (7)0.68267 (19)0.0240 (4)
H60.06570.14620.75460.029*
C70.11018 (7)0.07033 (7)0.63576 (18)0.0214 (3)
C80.17119 (7)0.06510 (7)0.59077 (18)0.0205 (3)
C90.19457 (7)0.01012 (7)0.52115 (18)0.0202 (3)
C100.25447 (7)0.00473 (8)0.45215 (19)0.0241 (4)
H100.28250.03840.46120.029*
C110.27291 (7)−0.04800 (8)0.3725 (2)0.0254 (4)
H110.3122−0.05020.32140.030*
C120.23214 (7)−0.09846 (7)0.36885 (19)0.0232 (4)
C130.17471 (7)−0.09597 (7)0.44037 (19)0.0208 (3)
C140.15216 (7)−0.04141 (7)0.51354 (18)0.0195 (3)
C150.09034 (7)−0.03480 (7)0.56703 (18)0.0212 (3)
H150.0635−0.06950.56440.025*
C160.06846 (7)0.02078 (7)0.62255 (18)0.0215 (3)
H160.02620.02570.65130.026*
C170.23450 (8)−0.16132 (8)0.2891 (2)0.0257 (4)
H170.2769−0.17690.26370.031*
C180.14564 (7)−0.15878 (7)0.4099 (2)0.0244 (4)
H180.1137−0.17140.49100.029*
C190.18458 (8)−0.10055 (8)0.04906 (19)0.0268 (4)
C200.18801 (7)−0.16089 (8)0.1424 (2)0.0263 (4)
H200.1949−0.19690.06880.032*
C210.12505 (8)−0.16503 (8)0.2289 (2)0.0252 (4)
H210.1045−0.20560.20820.030*
C220.08744 (8)−0.11216 (8)0.16359 (19)0.0246 (4)
C230.10842 (8)−0.01442 (7)0.01244 (19)0.0260 (4)
H23A0.0646−0.0134−0.02190.031*
H23B0.1344−0.0019−0.08050.031*
C240.11844 (8)0.02956 (8)0.1539 (2)0.0275 (4)
H24A0.09200.01600.24510.033*
H24B0.16200.02610.18960.033*
C250.10459 (8)0.09703 (8)0.1186 (2)0.0266 (4)
H25A0.13080.11180.02840.032*
H25B0.06070.10190.08680.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0261 (7)0.0423 (8)0.0323 (7)0.0000 (5)0.0082 (5)0.0044 (5)
O20.0228 (7)0.0364 (7)0.0334 (7)−0.0002 (5)−0.0026 (5)0.0081 (5)
O30.0297 (7)0.0280 (7)0.0240 (6)−0.0019 (5)−0.0018 (5)−0.0028 (5)
O40.0274 (7)0.0232 (6)0.0313 (7)0.0046 (5)0.0033 (5)0.0054 (5)
O50.0330 (7)0.0468 (8)0.0399 (8)0.0089 (6)0.0131 (6)0.0141 (6)
O60.0237 (7)0.0353 (7)0.0394 (7)0.0039 (5)0.0034 (5)−0.0018 (5)
N10.0226 (7)0.0226 (7)0.0229 (7)0.0004 (6)−0.0001 (5)0.0039 (5)
N20.0247 (7)0.0271 (8)0.0214 (7)0.0053 (6)0.0007 (5)0.0001 (6)
C10.0235 (9)0.0224 (9)0.0273 (9)−0.0010 (7)0.0014 (7)0.0081 (7)
C20.0228 (9)0.0205 (8)0.0273 (9)−0.0022 (6)0.0000 (6)0.0021 (6)
C30.0245 (9)0.0199 (9)0.0264 (9)0.0010 (6)0.0012 (6)0.0019 (6)
C40.0226 (9)0.0202 (8)0.0267 (9)0.0029 (7)0.0002 (7)0.0093 (6)
C50.0227 (9)0.0241 (9)0.0254 (9)−0.0003 (7)−0.0014 (7)0.0003 (6)
C60.0225 (9)0.0264 (9)0.0231 (8)−0.0014 (7)0.0003 (6)−0.0007 (7)
C70.0255 (9)0.0248 (9)0.0140 (8)0.0013 (7)0.0000 (6)0.0035 (6)
C80.0224 (8)0.0213 (8)0.0178 (8)−0.0006 (6)−0.0035 (6)0.0041 (6)
C90.0194 (8)0.0229 (8)0.0184 (8)0.0006 (6)−0.0032 (6)0.0050 (6)
C100.0183 (8)0.0265 (9)0.0275 (9)−0.0018 (7)−0.0021 (6)0.0059 (7)
C110.0189 (9)0.0288 (9)0.0284 (9)0.0017 (7)0.0017 (6)0.0063 (7)
C120.0238 (9)0.0241 (9)0.0216 (8)0.0042 (7)0.0001 (6)0.0052 (6)
C130.0210 (8)0.0216 (8)0.0197 (8)0.0010 (6)−0.0009 (6)0.0036 (6)
C140.0213 (8)0.0216 (8)0.0156 (8)−0.0006 (6)−0.0019 (6)0.0049 (6)
C150.0223 (8)0.0234 (9)0.0179 (8)−0.0034 (7)0.0000 (6)0.0039 (6)
C160.0199 (8)0.0272 (9)0.0174 (8)−0.0007 (6)0.0009 (6)0.0029 (6)
C170.0226 (9)0.0268 (9)0.0277 (9)0.0060 (7)0.0037 (7)0.0036 (7)
C180.0249 (9)0.0232 (9)0.0251 (9)0.0020 (7)0.0024 (7)0.0027 (6)
C190.0261 (9)0.0330 (10)0.0213 (8)0.0059 (7)0.0030 (7)−0.0013 (7)
C200.0274 (9)0.0250 (9)0.0266 (9)0.0041 (7)0.0028 (7)−0.0028 (7)
C210.0264 (9)0.0224 (9)0.0268 (9)0.0008 (7)0.0002 (7)−0.0030 (7)
C220.0248 (9)0.0269 (9)0.0220 (8)0.0010 (7)−0.0005 (7)−0.0066 (6)
C230.0280 (9)0.0288 (9)0.0213 (8)0.0062 (7)−0.0018 (7)0.0034 (7)
C240.0339 (10)0.0275 (9)0.0210 (9)0.0040 (7)−0.0036 (7)0.0035 (7)
C250.0305 (9)0.0278 (9)0.0214 (9)0.0023 (7)−0.0016 (7)0.0040 (7)

Geometric parameters (Å, °)

O1—C11.212 (2)C10—C111.376 (2)
O2—C41.212 (2)C10—H100.9500
O3—C51.452 (2)C11—C121.404 (2)
O3—C61.453 (2)C11—H110.9500
O4—C181.451 (2)C12—C131.377 (2)
O4—C171.450 (2)C12—C171.512 (2)
O5—C191.212 (2)C13—C141.413 (2)
O6—C221.213 (2)C13—C181.518 (2)
N1—C11.386 (2)C14—C151.416 (2)
N1—C41.392 (2)C15—C161.371 (2)
N1—C251.465 (2)C15—H150.9500
N2—C221.384 (2)C16—H160.9500
N2—C191.391 (2)C17—C201.575 (2)
N2—C231.461 (2)C17—H171.0000
C1—C21.503 (2)C18—C211.567 (2)
C2—C31.544 (2)C18—H181.0000
C2—C51.563 (2)C19—C201.518 (2)
C2—H21.0000C20—C211.541 (2)
C3—C41.508 (2)C20—H201.0000
C3—C61.567 (2)C21—C221.504 (2)
C3—H31.0000C21—H211.0000
C5—C81.525 (2)C23—C241.523 (2)
C5—H51.0000C23—H23A0.9900
C6—C71.514 (2)C23—H23B0.9900
C6—H61.0000C24—C251.518 (2)
C7—C81.376 (2)C24—H24A0.9900
C7—C161.406 (2)C24—H24B0.9900
C8—C91.415 (2)C25—H25A0.9900
C9—C101.420 (2)C25—H25B0.9900
C9—C141.445 (2)
C5—O3—C696.84 (11)C14—C13—C18132.49 (14)
C18—O4—C1796.65 (11)C13—C14—C15122.96 (14)
C1—N1—C4113.15 (14)C13—C14—C9116.35 (14)
C1—N1—C25122.21 (13)C15—C14—C9120.55 (14)
C4—N1—C25123.88 (13)C16—C15—C14121.27 (15)
C22—N2—C19113.30 (14)C16—C15—H15119.4
C22—N2—C23122.69 (13)C14—C15—H15119.4
C19—N2—C23122.87 (14)C15—C16—C7118.23 (14)
O1—C1—N1123.81 (16)C15—C16—H16120.9
O1—C1—C2127.59 (15)C7—C16—H16120.9
N1—C1—C2108.52 (13)O4—C17—C12100.93 (13)
C1—C2—C3105.10 (13)O4—C17—C20100.38 (13)
C1—C2—C5114.57 (13)C12—C17—C20107.96 (13)
C3—C2—C5101.47 (12)O4—C17—H17115.2
C1—C2—H2111.7C12—C17—H17115.2
C3—C2—H2111.7C20—C17—H17115.2
C5—C2—H2111.7O4—C18—C13101.20 (12)
C4—C3—C2104.59 (13)O4—C18—C2198.67 (12)
C4—C3—C6114.28 (13)C13—C18—C21110.69 (13)
C2—C3—C6101.62 (12)O4—C18—H18114.8
C4—C3—H3111.9C13—C18—H18114.8
C2—C3—H3111.9C21—C18—H18114.8
C6—C3—H3111.9O5—C19—N2123.13 (16)
O2—C4—N1123.67 (15)O5—C19—C20128.48 (15)
O2—C4—C3127.84 (15)N2—C19—C20108.39 (14)
N1—C4—C3108.46 (13)C19—C20—C21104.03 (13)
O3—C5—C8101.09 (12)C19—C20—C17115.30 (14)
O3—C5—C299.32 (12)C21—C20—C17101.97 (13)
C8—C5—C2109.09 (13)C19—C20—H20111.6
O3—C5—H5115.1C21—C20—H20111.6
C8—C5—H5115.1C17—C20—H20111.6
C2—C5—H5115.1C22—C21—C20105.53 (14)
O3—C6—C7101.01 (12)C22—C21—C18115.50 (13)
O3—C6—C3100.58 (12)C20—C21—C18100.74 (13)
C7—C6—C3107.61 (13)C22—C21—H21111.5
O3—C6—H6115.3C20—C21—H21111.5
C7—C6—H6115.3C18—C21—H21111.5
C3—C6—H6115.3O6—C22—N2123.74 (15)
C8—C7—C16122.16 (15)O6—C22—C21128.01 (16)
C8—C7—C6105.20 (13)N2—C22—C21108.25 (14)
C16—C7—C6132.46 (15)N2—C23—C24108.10 (13)
C7—C8—C9121.47 (14)N2—C23—H23A110.1
C7—C8—C5105.19 (13)C24—C23—H23A110.1
C9—C8—C5133.02 (14)N2—C23—H23B110.1
C8—C9—C10123.95 (15)C24—C23—H23B110.1
C8—C9—C14116.05 (14)H23A—C23—H23B108.4
C10—C9—C14119.89 (15)C25—C24—C23115.17 (13)
C11—C10—C9121.64 (15)C25—C24—H24A108.5
C11—C10—H10119.2C23—C24—H24A108.5
C9—C10—H10119.2C25—C24—H24B108.5
C10—C11—C12118.22 (15)C23—C24—H24B108.5
C10—C11—H11120.9H24A—C24—H24B107.5
C12—C11—H11120.9N1—C25—C24108.51 (13)
C13—C12—C11121.82 (15)N1—C25—H25A110.0
C13—C12—C17104.63 (14)C24—C25—H25A110.0
C11—C12—C17133.45 (15)N1—C25—H25B110.0
C12—C13—C14121.86 (15)C24—C25—H25B110.0
C12—C13—C18105.53 (14)H25A—C25—H25B108.4
C4—N1—C1—O1178.33 (15)C18—C13—C14—C15−4.6 (3)
C25—N1—C1—O17.9 (2)C12—C13—C14—C9−5.0 (2)
C4—N1—C1—C21.29 (18)C18—C13—C14—C9179.76 (15)
C25—N1—C1—C2−169.11 (13)C8—C9—C14—C13178.42 (13)
O1—C1—C2—C3179.59 (16)C10—C9—C14—C132.1 (2)
N1—C1—C2—C3−3.51 (16)C8—C9—C14—C152.7 (2)
O1—C1—C2—C5−69.9 (2)C10—C9—C14—C15−173.62 (14)
N1—C1—C2—C5106.97 (15)C13—C14—C15—C16−173.38 (15)
C1—C2—C3—C44.25 (16)C9—C14—C15—C162.0 (2)
C5—C2—C3—C4−115.36 (13)C14—C15—C16—C7−4.3 (2)
C1—C2—C3—C6123.42 (13)C8—C7—C16—C151.8 (2)
C5—C2—C3—C63.80 (15)C6—C7—C16—C15176.25 (16)
C1—N1—C4—O2−176.40 (14)C18—O4—C17—C1252.79 (14)
C25—N1—C4—O2−6.2 (2)C18—O4—C17—C20−57.98 (13)
C1—N1—C4—C31.60 (18)C13—C12—C17—O4−35.42 (15)
C25—N1—C4—C3171.81 (13)C11—C12—C17—O4148.25 (17)
C2—C3—C4—O2174.23 (15)C13—C12—C17—C2069.39 (16)
C6—C3—C4—O264.0 (2)C11—C12—C17—C20−106.9 (2)
C2—C3—C4—N1−3.66 (16)C17—O4—C18—C13−50.62 (13)
C6—C3—C4—N1−113.89 (14)C17—O4—C18—C2162.61 (13)
C6—O3—C5—C8−50.90 (13)C12—C13—C18—O430.01 (15)
C6—O3—C5—C260.80 (13)C14—C13—C18—O4−154.14 (16)
C1—C2—C5—O3−151.62 (13)C12—C13—C18—C21−73.82 (16)
C3—C2—C5—O3−38.98 (14)C14—C13—C18—C21102.04 (19)
C1—C2—C5—C8−46.38 (18)C22—N2—C19—O5−177.28 (16)
C3—C2—C5—C866.26 (15)C23—N2—C19—O5−9.2 (3)
C5—O3—C6—C752.06 (13)C22—N2—C19—C202.06 (18)
C5—O3—C6—C3−58.41 (13)C23—N2—C19—C20170.12 (14)
C4—C3—C6—O3144.55 (13)O5—C19—C20—C21173.59 (18)
C2—C3—C6—O332.53 (14)N2—C19—C20—C21−5.71 (17)
C4—C3—C6—C739.30 (18)O5—C19—C20—C1762.8 (2)
C2—C3—C6—C7−72.71 (15)N2—C19—C20—C17−116.47 (15)
O3—C6—C7—C8−33.94 (15)O4—C17—C20—C19142.32 (13)
C3—C6—C7—C871.00 (15)C12—C17—C20—C1937.14 (18)
O3—C6—C7—C16150.96 (16)O4—C17—C20—C2130.35 (14)
C3—C6—C7—C16−104.09 (18)C12—C17—C20—C21−74.84 (15)
C16—C7—C8—C93.1 (2)C19—C20—C21—C227.03 (17)
C6—C7—C8—C9−172.63 (14)C17—C20—C21—C22127.24 (13)
C16—C7—C8—C5177.36 (13)C19—C20—C21—C18−113.47 (14)
C6—C7—C8—C51.63 (16)C17—C20—C21—C186.74 (15)
O3—C5—C8—C731.17 (15)O4—C18—C21—C22−154.94 (13)
C2—C5—C8—C7−72.85 (16)C13—C18—C21—C22−49.42 (18)
O3—C5—C8—C9−155.52 (16)O4—C18—C21—C20−41.83 (14)
C2—C5—C8—C9100.45 (19)C13—C18—C21—C2063.69 (15)
C7—C8—C9—C10170.97 (14)C19—N2—C22—O6−178.31 (15)
C5—C8—C9—C10−1.5 (3)C23—N2—C22—O613.6 (2)
C7—C8—C9—C14−5.2 (2)C19—N2—C22—C212.70 (19)
C5—C8—C9—C14−177.62 (15)C23—N2—C22—C21−165.38 (13)
C8—C9—C10—C11−173.83 (15)C20—C21—C22—O6174.90 (16)
C14—C9—C10—C112.2 (2)C18—C21—C22—O6−74.8 (2)
C9—C10—C11—C12−3.7 (2)C20—C21—C22—N2−6.16 (17)
C10—C11—C12—C130.8 (2)C18—C21—C22—N2104.13 (16)
C10—C11—C12—C17176.65 (16)C22—N2—C23—C2476.48 (19)
C11—C12—C13—C143.6 (2)C19—N2—C23—C24−90.46 (18)
C17—C12—C13—C14−173.23 (14)N2—C23—C24—C25178.61 (14)
C11—C12—C13—C18−179.96 (14)C1—N1—C25—C2476.11 (19)
C17—C12—C13—C183.17 (16)C4—N1—C25—C24−93.24 (17)
C12—C13—C14—C15170.65 (15)C23—C24—C25—N1−179.18 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2675).

References

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